CN108084192A - A kind of method that micro passage reaction carries out cyan-hydrolysis reaction - Google Patents
A kind of method that micro passage reaction carries out cyan-hydrolysis reaction Download PDFInfo
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- CN108084192A CN108084192A CN201711463244.3A CN201711463244A CN108084192A CN 108084192 A CN108084192 A CN 108084192A CN 201711463244 A CN201711463244 A CN 201711463244A CN 108084192 A CN108084192 A CN 108084192A
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 76
- 238000006460 hydrolysis reaction Methods 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 23
- 239000000463 material Substances 0.000 claims abstract description 24
- 230000007062 hydrolysis Effects 0.000 claims abstract description 23
- 239000002994 raw material Substances 0.000 claims abstract description 21
- -1 cyano class compound Chemical class 0.000 claims abstract description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
- 238000003860 storage Methods 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 229960000583 acetic acid Drugs 0.000 claims description 4
- 239000012362 glacial acetic acid Substances 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 16
- 239000002253 acid Substances 0.000 abstract description 15
- 239000003513 alkali Substances 0.000 abstract description 8
- 230000008569 process Effects 0.000 abstract description 7
- 230000035484 reaction time Effects 0.000 abstract description 6
- 238000012546 transfer Methods 0.000 abstract description 6
- 230000003321 amplification Effects 0.000 abstract description 4
- 238000003199 nucleic acid amplification method Methods 0.000 abstract description 4
- 238000007086 side reaction Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 2
- 238000005265 energy consumption Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 11
- 235000011121 sodium hydroxide Nutrition 0.000 description 11
- 238000005086 pumping Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 238000007600 charging Methods 0.000 description 8
- 238000001514 detection method Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000011067 equilibration Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 4
- AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- FCTXEFOUDMXDPD-UHFFFAOYSA-N 3-sulfanylpropanenitrile Chemical compound SCCC#N FCTXEFOUDMXDPD-UHFFFAOYSA-N 0.000 description 3
- IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 description 3
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 3
- 235000004279 alanine Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- DRAFVCKNYNQOKR-GFCCVEGCSA-N (1-methoxycarbonylcyclopropyl) 3-[(1r)-1-phenylethyl]imidazole-4-carboxylate Chemical class C=1N=CN([C@H](C)C=2C=CC=CC=2)C=1C(=O)OC1(C(=O)OC)CC1 DRAFVCKNYNQOKR-GFCCVEGCSA-N 0.000 description 2
- BUSOTUQRURCMCM-UHFFFAOYSA-N 3-Phenoxypropionic acid Chemical compound OC(=O)CCOC1=CC=CC=C1 BUSOTUQRURCMCM-UHFFFAOYSA-N 0.000 description 2
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical class OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- AYNKQZGCHPCINW-UHFFFAOYSA-N N1=C(C=CC=C1)CC#N.C1CCN2CCCC12 Chemical compound N1=C(C=CC=C1)CC#N.C1CCN2CCCC12 AYNKQZGCHPCINW-UHFFFAOYSA-N 0.000 description 2
- BGCKSKZOSRXXQW-UHFFFAOYSA-N N1=C(C=CC=C1)CC(=O)O.C1CCN2CCCC12 Chemical compound N1=C(C=CC=C1)CC(=O)O.C1CCN2CCCC12 BGCKSKZOSRXXQW-UHFFFAOYSA-N 0.000 description 2
- 150000007824 aliphatic compounds Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229940000635 beta-alanine Drugs 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- BCQTVJKBTWGHCX-UHFFFAOYSA-N pilsicainide Chemical compound CC1=CC=CC(C)=C1NC(=O)CC1(CCC2)N2CCC1 BCQTVJKBTWGHCX-UHFFFAOYSA-N 0.000 description 2
- 229950010769 pilsicainide Drugs 0.000 description 2
- KZMAWJRXKGLWGS-UHFFFAOYSA-N 2-chloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-n-(3-methoxypropyl)acetamide Chemical compound S1C(N(C(=O)CCl)CCCOC)=NC(C=2C=CC(OC)=CC=2)=C1 KZMAWJRXKGLWGS-UHFFFAOYSA-N 0.000 description 1
- IXAUFLAHUXISCH-UHFFFAOYSA-N 3-phenoxypropanenitrile Chemical compound N#CCCOC1=CC=CC=C1 IXAUFLAHUXISCH-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 244000144992 flock Species 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- ADRDEXBBJTUCND-UHFFFAOYSA-N pyrrolizidine Chemical compound C1CCN2CCCC21 ADRDEXBBJTUCND-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F33/00—Other mixers; Mixing plants; Combinations of mixers
- B01F33/30—Micromixers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0053—Details of the reactor
- B01J19/0073—Sealings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2415—Tubular reactors
- B01J19/2425—Tubular reactors in parallel
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B41/00—Formation or introduction of functional groups containing oxygen
- C07B41/08—Formation or introduction of functional groups containing oxygen of carboxyl groups or salts, halides or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/26—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing carboxyl groups by reaction with HCN, or a salt thereof, and amines, or from aminonitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
- C07C319/12—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by reactions not involving the formation of mercapto groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00054—Controlling or regulating the heat exchange system
- B01J2219/00056—Controlling or regulating the heat exchange system involving measured parameters
- B01J2219/00058—Temperature measurement
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Abstract
The invention discloses a kind of methods that the reaction of cyano class compound hydrolysis is carried out based on micro passage reaction, the compound containing cyano group carries out cyan-hydrolysis class reaction under the action of alkalescence or acid and alkali substance using micro passage reaction specifically in molecule.In present invention process the uniform mixing of raw material moment and efficient heat transfer are realized using micro passage reaction;When solving most important cyano class compound and being hydrolyzed using alkali, slug present in production process is dangerous;The equivalent proportion of material in reaction process is also reduced simultaneously;Reduce side reaction;And dozens of minutes will be foreshortened to the reaction time even tens seconds.In a word, present invention process improves the security of operation, realizes the safety amplification production of cyano class compound, and shortens the reaction time of cyano class compound hydrolysis, improve the selectivity and reaction efficiency of reaction, reduce the energy consumption in production, improve the utilization rate of raw material, make production process more environmentally friendly, low production cost, meanwhile use that occupation area of equipment is small, production capacity is high, greatly improve production efficiency and ability.
Description
Technical field
The present invention relates to a kind of method that micro passage reaction carries out cyan-hydrolysis reaction, specifically in microchannel plate
It answers in device and reaction is hydrolyzed containing cyano group and lye or acid solution in molecule, generate the compound containing carboxyl, belong to
Organic synthesis field.
Background technology
Micro-reacting tcchnology originates from the last century 90's, and the advantage of microreactor gradually highlights in recent years, and recognizes
Microreactor is better than conventional mass-and heat-transfer ability, and microreactor then is applied to the field of chemical synthesis;Microreactor develops
To today, oneself changes liquid flow pattern by reaction channel and forms infinitesimal ruler through no longer pursuing the small of reaction channel merely
The liquid stream of degree forms efficiently quick mass-and heat-transfer.Using these advantages, can be very good to solve to ask present in popular response
Topic.
Such as cyan-hydrolysis reaction in popular response, carried out under conditions of acid or alkalescence, cyano class compound water first
Solution generation amide, the reaction was continued ultimately produces carboxylic acid or carboxylate.Cyano class compound is all in pesticide, dyestuff and medical domain
A kind of important organic synthesis intermediate can not only hydrolyze preparation acid, can also be reduced into amine, be prepared as aminopropionitrile hydrolyzes
Beta-alanine, it is more extensive in the application of chemical industry synthesis field, and with important application value.This kind of reaction normal conditions are in alkali
Property under the conditions of hydrolysis can be relatively complete, and cannot react thorough under acid condition, under normal temperature and pressure conditions cyan-hydrolysis when
Between it is longer, hydrolysis efficiency is low, and often reaction cannot be carried out thoroughly, and obtained the mixture of amide and carboxylic acid, made what is finally obtained
Product purity is inadequate, therefore just needs to improve the temperature and acid-base value of hydrolysis, especially under common alkaline condition, improves temperature
The violent aerogenesis of meeting, it is difficult to control reaction, risk is bigger;And it is carried out not exclusively under popular response acid condition, it is necessary to increase
Acid amount, these excessive soda acids also need to be neutralized, and cause unnecessary waste and environmental pollution.
The content of the invention
Present invention is generally directed to it is above-mentioned it is conventional carry out cyan-hydrolysis reaction when can there are the problem of, it is proposed that one kind is more pacified
Entirely, economic, environmental protection hydrolysis preparation process.We utilize the quick mixed material of micro passage reaction, quick separating, efficiently
The characteristic of mass-and heat-transfer carry out such hydrolysis and achieve more excellent effect;Improve the conversion ratio of reaction, while by
It is rapidly separated in reacting rear material, reduces the generation of side reaction, and reaction end can be controlled well;Even more important
It is, using microreactor, to avoid in popular response using the danger of alkali high temperature and high pressure hydrolysis reaction slug, decrease use
The equivalents that acid is hydrolyzed, this has been considerably improved industrial security and feasibility;Meanwhile closed reaction system
Also safety guarantee is provided for operating personnel.
The present invention has carried out a series of cyano compound in acidity in micro passage reaction in order to achieve the above object
Or the reaction being hydrolyzed under alkaline condition.More importantly lab scale and zero amplification of amplification production can be realized using microreactor
Effect, thus such hydrolysis present invention studied after can be amplified production without involving an inventive effort.This hair
The bright technical solution used for:
A kind of method that micro passage reaction carries out cyan-hydrolysis reaction contains the change of cyano group (- C ≡ N) in molecule
It closes object in a solvent, adds in alkalescence or acidic materials, using microreactor system under the conditions of 0-150 DEG C, 0.1-10Mpa, into
The reaction of row hydrolysis.
Further, the compound containing cyano group (- C ≡ N) is aliphatic compound in the molecule.Preferably
Straight chain or annular at least containing there are one the aliphatic compounds of cyano containing 3-14 carbon atom;
Further, the cyano group of reaction can be hydrolyzed there are one at least containing in compound structure.
Further, alkaline matter in sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate or other alkali at least
It is a kind of.Basic hydrolysis can avoid violent aerogenesis to avoid reaction slug.
Further, acidic materials are at least one of sulfuric acid, hydrochloric acid, phosphoric acid or other acid.With popular response phase
Compare, the usage amount of acid can be greatly reduced.
Further, solvent is water, alcohols, glacial acetic acid or other organic solvents.
Further, the molar ratio of the compound containing cyano group (- C ≡ N) and alkalescence or acidic materials is in molecule
1:1-6, wherein preferably 1:1-1.05.
Further, preferred 80-120 DEG C of reaction temperature.
Further, hydrolysis time 0.1s-60min, wherein it is preferred that time 1-15min.
Further, the preferred pressure of reaction pressure is 1-5MPa.
Further, the micro channel reactor system includes the constant flow pump being sequentially communicated, micro-mixer, tubulation reaction
Device, heat exchanger, it is described to be placed in constant temperature bath.
Further, micro channel reactor system includes:Raw material storage tank 2, feed pump 2, micro-mixer 1 (can appoint
Selected from CPMM series, SIMM series, Starlam series), shell-and-tube reactor 1 (preferably stainless steel), 3, heat exchanger, temperature
Degree probe 5, temperature indicator 1, counterbalance valve 1, receiving tank 1;
The operating process of cyan-hydrolysis reaction is preferably carried out using micro passage reaction:
1) microreactor system is attached;
2) by micro passage reaction by counterbalance valve back pressure, pressure is reached in micro channel reactor system;
3) micro-mixer U and shell-and-tube reactor, heat exchanger are warming up to reaction temperature by constant temperature bath;
4) system balancing and calibration;
5) raw material and catalyst are fed through feed pump, are mixed in micro-mixer, through shell-and-tube reactor, heat exchanger certain
At a temperature of, condensation reaction is completed in certain time;
6) material that reaction is completed enters receiving tank storage at lower temperature, waits to post-process;
7) termination of pumping, cleaning system send material to vapor detection.
It compares with the prior art, the present invention has following advantageous effect:
Micro passage reaction is closed system, can avoid contact with harmful substance;The present invention can realize the quick of material
Contact, then moment chemically react, will shorten in the reaction time thousands of times;It can be very good to carry out mass-and heat-transfer, avoid
Using the danger of alkali high temperature and high pressure hydrolysis reaction slug in popular response, industrial security and feasibility are improved;Subtract
Lack the equivalents that cyan-hydrolysis is carried out using acid or alkaline matter, avoided and excessive soda acid is adjusted after having reacted, reduce life
Produce cost, safety and environmental protection;The reaction time is accurately controlled, quick separating can be quenched, avoided from system after the completion of reaction
Side reaction occurs, and improves percent hydrolysis.
In present invention process the uniform mixing of raw material moment and efficient heat transfer are realized using micro passage reaction;It solves most
When main cyano class compound is hydrolyzed using alkali, slug present in production process is dangerous;Also reduce reaction simultaneously
The equivalent proportion of material in the process;Reduce side reaction;And dozens of minutes will be foreshortened to the reaction time even tens seconds.Always
It, present invention process improves the security of operation, realizes the safety amplification production of cyano class compound, and shortens
The reaction time of cyano class compound hydrolysis improves the selectivity and reaction efficiency of reaction, and the energy reduced in production disappears
Consumption, improves the utilization rate of raw material, makes production process more environmentally friendly, low production cost, meanwhile, use occupation area of equipment
It is small, production capacity is high, greatly improve production efficiency and ability.
Description of the drawings
Fig. 1 is present invention process flow chart
Sequence number | Letter | Explanation | Sequence number | Letter | Explanation |
1 | P=XX | Pump | 7 | TI-XX | Thermometer |
2 | V-XX | Charging/receiving tank | 8 | BPV-XX | Counterbalance valve |
3 | F-XX | Filter | 9 | PG-XX | Pressure gauge |
4 | PT-XX | Pressure transmitter | 10 | CV-XX | Check valve |
5 | R-XX | Reactor | 11 | HEX-XX | Heat exchanger |
6 | T-XX | Rectifying column |
Raw material storage tank V-01, V-02;Product pans V-03;Feed pump P-01, P-02;Micro- heat exchanger HEX-01, HEX-
02、HEX-03;Micro-mixer MI-01;Stainless steel shell-and-tube reactor R-01;Counterbalance valve BVP-01;Temp probe TI-01, TI-
02、TI-03、TI-04、TI-05。
Raw material storage tank v-01 connection feed pumps p-01 enters heat exchanger HEX-01 (for heating raw material), raw material storage tank v-
02 connection feed pump p-02 enters heat exchanger HEX-02 (for heating raw material), the reaction solution come out from HEX-01 and HEX-02
Into micro-mixer MI-01, shell-and-tube reactor R-01 is then flowed sequentially through, heat exchanger HEX-03 (is used to cool down to reaction solution),
Eventually enter into receiving tank V-03.
Specific embodiment
Following non-limiting examples can make those of ordinary skill in the art be more fully understood the present invention, but not with
Any mode limits the present invention.Reagent and material described in following embodiments, unless otherwise specified, are commercially obtained
, the present invention can carry out cyan-hydrolysis this one kind reaction, and such reaction is not limited only to described in embodiment with alkali or acid, after
Processing method is also not limited to described in the embodiment of the present invention, specifically gives representational embodiment.
As shown in Figure 1, micro channel reactor system includes raw material storage tank 2, feed pump 2, micro-mixer 1 (can appoint
Selected from CPMM series, SIMM series, Starlam series), stainless steel shell-and-tube reactor 1,3, heat exchanger, temp probe 5,
Temperature indicator 1, counterbalance valve 1, receiving tank 1.
Temp probe TI-01 is used to test the temperature of HEX-01 outlets liquid;Temp probe TI-02 is used to test HEX-
The temperature of 02 outlet liquid;Temp probe TI-03 is used to test the temperature of MI-01 outlets liquid;Temp probe TI-04 is used for
Test the temperature of R-01 outlets liquid;Temp probe TI-05 is used to test the temperature of HEX-03 outlets liquid;5 temp probes
It is connected on temperature indicator.
Embodiment 1
It is prepared by Beta-alanine:With 80% aminopropionitrile of content (technical grade) aqueous solution;30% sodium hydroxide of content is water-soluble
Liquid is raw material.
Technological operation step:
1) connection of micro-reactor apparatus:All devices are connected as shown in Figure 1, use Starlam3000 microreactors;
2) debugging of micro-reactor apparatus:Constant temperature circulating machine is opened, 110 DEG C of set temperature is injected by constant flow pump water micro-
In consersion unit, micro-reactor apparatus internal duct 10min is cleaned, opening simultaneously counterbalance valve makes system back pressure 5.0MPa, and inspection is set
No leakage, gas leak phenomenon are had, whether numerical value is accurate for temperature, pressure monitor equipment, is carried out in next step after all are errorless;
3) flux modification of constant flow pump:Using water as medium calibrated flow, error is no more than setting value by constant flow pump P01, P02
1%;
4) prepare:Aminopropionitrile solution 10g storage tanks are connected to constant flow pump P01,10% sodium hydroxide solution 56.56g storage
Tank is connected to constant flow pump P02, and the microreactor inlet temperature of sodium hydrate aqueous solution all the way is 100 DEG C, microreactor outlet temperature
108 DEG C of degree, after equilibration time 5min, reaction temperature rises to 110 DEG C, starts charging reaction;
5) mixed in micro-mixer U, through shell-and-tube reactor, heat exchanger, time 1.5min completes hydrolysis;
6) material that reaction is completed enters receiving tank V-03, and vapor detection, aminopropionitrile conversion ratio are sent in cooling stirring
99.9%;
7) separation is neutralized:By alanine sodium water solution by ion exchange column, neutralization reaction and desalination are carried out, obtains ammonia
Base propionic acid aqueous solution;
8) crystallization filters:Alanine aqueous solution is evaporated under reduced pressure and is removed water, white crystal i.e. alanine is obtained by filtration
12.45g product yield:98%;
9) micro-reactor apparatus cleans:Constant temperature circulating machine is closed, micro-reactor apparatus pipeline is rinsed with water by constant flow pump
10min;
Embodiment 2
It is prepared by 3- mercaptopropionic acids:With the 3- sulfydryl propionitrile of content 95%, 20% hydrochloric acid solution is raw material without using solvent.
Technological operation step:
1) microreactor system is attached, and debugs same aforesaid operations;
2) prepare:The 3- sulfydryl propionitrile 5g that content is 95% is placed in holding vessel V-01 and is stored, by pumping P-01 chargings;It will
20% hydrochloric acid solution 10.92g is placed in storage in holding vessel V-02 and is fed by pumping P-02, to the microreactor entrance of hydrochloric acid solution
Temperature is 110 DEG C, 114 DEG C of microreactor outlet temperature, and after equilibration time 5min, reaction temperature rises to 115 DEG C, starts to connect
Material;
3) mixed in micro-mixer U, through shell-and-tube reactor, heat exchanger, time 1min completes hydrolysis;
4) material that reaction is completed enters receiving tank V-03, and cooling stirring send vapor detection, to 3- sulfydryl propionitrile conversion ratios
99.99%;
5) be concentrated under reduced pressure water outlet, distills out product 3- mercaptopropionic acids 5.2g;
6) micro-reactor apparatus cleans:Constant temperature circulating machine is closed, micro-reactor apparatus pipeline is rinsed with water by constant flow pump
10min。
Embodiment 3
It is prepared by 7 Α-double pyrrolizidine pyridine-acetic acid:With 7 Α of Pilsicainide intermediate-double pyrrolizidine pyridine-acetonitrile, 36% salt
Acid solution is raw material.
Technological operation step:
1) microreactor system is attached, and debugs same aforesaid operations;
2) prepare:7 Α of Pilsicainide intermediate-double pyrrolizidine pyridine-acetonitrile 10g that content is 95% is placed in holding vessel
Storage in V-01, by pumping P-01 chargings;By 36% hydrochloric acid solution 14.13g be placed in holding vessel V-02 storage by pump P-02 into
Material, the microreactor inlet temperature of hydrochloric acid solution all the way are 100 DEG C, 103 DEG C of microreactor outlet temperature, equilibration time 5min
Afterwards, reaction temperature rises to 105 DEG C, starts splicing;
3) mixed in micro-mixer U, through shell-and-tube reactor, heat exchanger, time 3min completes hydrolysis;
4) material that reaction is completed enters receiving tank V-03, and vapor detection, 7 Α-double pyrrolizidine pyridine-second are sent in cooling stirring
Nitrile conversion ratio 95%;
5) 10~15 DEG C are cooled to, there is solid precipitation, the hydrochloride of 7 Α of product-double pyrrolizidine pyridine-acetic acid is obtained by filtration
12.35g;
6) micro-reactor apparatus cleans:Constant temperature circulating machine is closed, micro-reactor apparatus pipeline is rinsed with water by constant flow pump
10min。
Embodiment 4
It is prepared by 2- amino -2,3- acid dimethyls:With the 2- amino -2,3- nitrile dimethyls of content 95%, 95% it is dense
Sulfuric acid is raw material.
Technological operation step:
1) microreactor system is attached, and debugs same aforesaid operations;
2) prepare:2- amino -2,3- nitrile dimethyls 10g that content is 95% is placed in storage in holding vessel V-01, by
Pump P-01 chargings;95% concentrated sulfuric acid solution 9.87g is placed in storage in holding vessel V-02 to be fed by pumping P-02, concentrated sulfuric acid solution
Microreactor inlet temperature all the way is 100 DEG C, 98 DEG C of microreactor outlet temperature, after equilibration time 5min, in reaction temperature
100 DEG C are risen to, starts splicing;
3) mixed in micro-mixer U, through shell-and-tube reactor, heat exchanger, time 0.5min completes hydrolysis;
4) material that reaction is completed enters receiving tank V-03, and vapor detection, 2- amino -2,3- dimethyl are sent in cooling stirring
Butyronitrile conversion ratio 99%;
5) near 20~30 DEG C of temperature with ammonium hydroxide tune pH value extremely in alkalescent, with Toluene extractive reaction liquid, concentrate toluene,
Obtain product 2- amino -2,3- amide dimethyl butyrates 11.48g.
6) micro-reactor apparatus cleans:Constant temperature circulating machine is closed, micro-reactor apparatus pipeline is rinsed with water by constant flow pump
10min。
Embodiment 5
The preparation of phenylacetic acid:Using 98% benzene acetonitrile of content, 10% sodium hydroxide as raw material.
Technological operation step:
1) microreactor system is attached, and debugs same aforesaid operations;
2) prepare:The benzene acetonitrile 10g that mass content is 98% is placed in holding vessel V-01 and is stored, by pumping P-01 chargings;
10.0% sodium hydroxide solution 86mmol is placed in storage in holding vessel V-02 to be fed by pumping P-02, sodium hydrate aqueous solution one
The microreactor inlet temperature on road is 100 DEG C, 102 DEG C of microreactor outlet temperature, after equilibration time 5min, in reaction temperature
105 DEG C are risen to, starts splicing;
3) mixed in micro-mixer U, through shell-and-tube reactor, heat exchanger, time 1min completes hydrolysis;
4) material that reaction is completed enters receiving tank V-03, and vapor detection, benzene acetonitrile conversion ratio are sent in cooling stirring
98.9%;
5) there is product precipitation after being adjusted to PH=1~2 with hydrochloric acid after stirring 30min, centrifuge, obtain product 11.27g, product is received
Rate 97%;
6) micro-reactor apparatus cleans:Constant temperature circulating machine is closed, micro-reactor apparatus pipeline is rinsed with water by constant flow pump
10min;
Embodiment 6
Preparation to sodium chloroacetate:Using 98% p-chlorobenzyl cyanide of content, 10% sodium hydroxide solution as raw material.
Technological operation step:
1) microreactor system is attached, and debugs same aforesaid operations;
2) prepare:The p-chlorobenzyl cyanide 8g that mass content is 98% is placed in holding vessel V-01 and stores, by pump P-01 into
Material;10.0% sodium hydroxide solution 21.41g is placed in storage in holding vessel V-02, and, by pumping P-02 chargings, sodium hydroxide is water-soluble
The microreactor inlet temperature of liquid all the way is 110 DEG C, 112 DEG C of microreactor outlet temperature, after equilibration time 5min, reaction temperature
Degree rises to 116 DEG C, starts splicing;
3) mixed in micro-mixer U, through shell-and-tube reactor, heat exchanger, time 3min completes hydrolysis;
4) material that reaction is completed enters receiving tank V-03, and vapor detection, p-chlorobenzyl cyanide conversion ratio are sent in cooling stirring
99.99%;
5) PH=1~2 are adjusted to hydrochloric acid, have product precipitation after stirring 30min, centrifuged, obtain product 8.91g, product yield
99%;
6) micro-reactor apparatus cleans:Constant temperature circulating machine is closed, micro-reactor apparatus pipeline is rinsed with water by constant flow pump
10min。
Embodiment 7
It is prepared by beta-phenoxy propionic acid:With the 3- phenoxypropionitriles of content 98%, 36% concentrated hydrochloric acid, for raw material, glacial acetic acid
Make solvent.
Technological operation step:
1) microreactor system is attached, and debugs same aforesaid operations;
2) prepare:The 3- phenoxypropionitriles 10g that content is 98% is dissolved in 20mL glacial acetic acid, is placed in holding vessel V-01
Interior storage, by pumping P-01 chargings;By 36% concentrated hydrochloric acid solution 7.15g, it is placed in storage in holding vessel V-02 and is fed by pumping P-02,
The microreactor inlet temperature of concentrated hydrochloric acid solution all the way is 100 DEG C, 98 DEG C of microreactor outlet temperature, after equilibration time 5min,
Reaction temperature rises to 100 DEG C, starts splicing;
3) mixed in micro-mixer U, through shell-and-tube reactor, heat exchanger, time 2min completes hydrolysis;
4) material that reaction is completed enters receiving tank V-03, and vapor detection, 3- phenoxypropionitrile conversion ratios are sent in cooling stirring
98%;
5) near 20~30 DEG C of temperature, are diluted with cold water, obtain white flock beta-phenoxy propionic acid crude product 10.73g.
6) micro-reactor apparatus cleans:Constant temperature circulating machine is closed, micro-reactor apparatus pipeline is rinsed with water by constant flow pump
10min;
Claims (10)
1. a kind of method that micro passage reaction carries out the reaction of cyano class compound hydrolysis, it is characterised in that:Contain cyanogen in molecule
The compound of base group (- C ≡ N) in a solvent, adds in alkalescence or acidic materials, using micro channel reactor system in 0-150
DEG C, under the conditions of 0.1-10Mpa, the reaction that is hydrolyzed.
2. according to the method described in claim 1, the compound containing cyano group (- C ≡ N) is aliphatic in the molecule
Compound.
3. according to the method described in claim 1, it is characterized in that:Contain cyano group (- C ≡ N) compound in the molecule
Structure at least contain that there are one the cyano group of reaction can be hydrolyzed.
4. according to the method described in claim 1, it is characterized in that:The alkaline matter is sodium hydroxide, potassium hydroxide, carbonic acid
One in sodium, potassium carbonate at least plants.
5. according to the method described in claim 1, it is characterized in that:The acidic materials are sulfuric acid, hydrochloric acid, in phosphoric acid at least
It is a kind of.
6. according to the method described in claim 1, it is characterized in that:The solvent is water, alcohols or glacial acetic acid.
7. according to the method described in claim 1, it is characterized in that:Micro- reaction system includes the raw material being sequentially communicated storage
Tank, feed pump, heat exchanger, micro-mixer, shell-and-tube reactor, heat exchanger.
8. according to the method described in claim 1, it is characterized in that:By micro passage reaction by counterbalance valve back pressure, microchannel plate
It answers and reaches pressure in device system, raw material is fed through feed pump, is mixed in micro-mixer, through shell-and-tube reactor, heat exchanger one
Determine to complete hydrolysis class reaction at temperature.
9. according to the method described in claim 1, it is characterized in that:In molecule containing cyano group (- C ≡ N) compound with
Alkalescence or the molar ratio of acidic materials are 1:1-6.
10. according to the method described in claim 1, it is characterized in that:The reaction of the hydrolysis is 0.1s-60min.
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